Prior art patents describe polyethyleneimine reacted with polyester chains. These include U.S. Pat. No. 4,224,212 which describes a polyester with hydroxystearic acid or ricinoleic acid repeat units. U.S. Pat. No. 5,700,395 describes a polyester with caprolactone, hydroxystearic acid and/or ricinoleic acid repeat units. U.S. Pat. No. 4,861,380 describes a polyester from caprolactone. U.S. Pat. No. 6,197,877 describes a polyester from both caprolactone and valerolactone.
U.S. Pat. No. 7,767,750 describes a composition of a particulate solid, an organic media or water, and a compound that is the residue of a polyamine or polyimine, a dibasic acid, and an amine terminated poly(alkylenoxy).
WO2007/060070 and US2006/0183815 discloses amine-functional polymers reacted with one or more polyester polymeric chains in combination with one or more polyether chains, which has an amine reactive group, such as phosphate or carboxylate functionality, to make a dispersant.
U.S. Pat. No. 6,111,054 discloses a dispersing agent obtained by salt formation of an amine functional compound with an acid compound and more specifically combining a polyamine with at least three amino groups with a compound containing a phosphoric acid group, a sulphuric or sulphonic acid group in which the acid groups were attached to radicals by an ester functionality and the radicals were made up of polyester, polyether or polyurethanes or mixtures thereof.
WO2011/139580 published November 2011 relates to a (meth)acrylic polymer functionalized with poly(alkyleneoxy) segments used as a dispersant. WO2012/125609 published March 2012 relates to a polymer from polymerizing a mono-vinyl monomer with one or more carboxylic acid groups to form a polymer and reacting that polymer with a primary hydrocarbylamine and a poly(oxyalkylene) primary amine.
“Physicochemical properties of pH-controlled polyion complex (PIC) micelles of poly(acrylic acid)-based double hydrophilic block copolymers and various polyamines” in Analytical and Bioanalytical Chemistry (year 2012), 403(5), page 1395-1404, by J. Warnat, N. Marcotte, J. Reboul, G. Layrac, A. Aqil, C. Jerome, D. A. Lerner and C. Gerardin; discusses polymers of poly(acrylic acid)-b-poly(acrylate methoxy poly(ethylene oxide)) with linear poly(ethylene imine) hydrochloride.
US2013/0018121 and US2012/0029104 are patent publications to Byk Chemie.